2Me SiR600 | 1394003-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2Me SiR600
• 英文别名: 3-Imino-5,5-dimethyl-10-(2-methylphenyl)benzo[b][1]benzosilin-7-amine;2,2,2-trifluoroacetic acid；3-imino-5,5-dimethyl-10-(2-methylphenyl)benzo[b][1]benzosilin-7-amine;2,2,2-trifluoroacetic acid
• CAS: 1394003-20-3
• 化学式: C₂HF₃O₂*C₂₂H₂₂N₂Si
• 分子量: 456.54
• InChiKey: YCXYVVCILJZMIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  87.2
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2Me SiR600 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 Leu-SiR600
  参考文献：
  名称：

  Red fluorescent scaffold for highly sensitive protease activity probes

  摘要：

  We have developed a novel red fluorescent dye, 2Me SiR600 (lambda(em) = 613 nm), in which the O atom of Rhodamine Green at the 10 position of the xanthene moiety is replaced with a Si atom, as a scaffold for probes to detect protease activity with extremely high S/N ratio. As proof of concept, we designed and synthesized probes for caspase-3 activity (Z-DEVD-SiR600) and leucine aminopeptidase activity (Leu-SiR600). Caspase-3-mediated cleavage of Z-DEVD-SiR600 resulted in a large bathochromic shift (93 nm) of the absorption maximum and a 432-fold fluorescence enhancement. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.114
• 作为产物：
  描述：

  Z-DEVD-SiR600 在 3-[(3-cholamidopropyl)dimethylammonio]propanesulfonate 、 甘油 、 sodium chloride 、 1,4-二巯基-2,3-丁二醇 、 caspase-3 作用下， 以 二甲基亚砜 为溶剂， 生成 2Me SiR600
  参考文献：
  名称：

  Red fluorescent scaffold for highly sensitive protease activity probes

  摘要：

  We have developed a novel red fluorescent dye, 2Me SiR600 (lambda(em) = 613 nm), in which the O atom of Rhodamine Green at the 10 position of the xanthene moiety is replaced with a Si atom, as a scaffold for probes to detect protease activity with extremely high S/N ratio. As proof of concept, we designed and synthesized probes for caspase-3 activity (Z-DEVD-SiR600) and leucine aminopeptidase activity (Leu-SiR600). Caspase-3-mediated cleavage of Z-DEVD-SiR600 resulted in a large bathochromic shift (93 nm) of the absorption maximum and a 432-fold fluorescence enhancement. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.114

文献信息

• GLUTATHIONE-DETECTING FLUORESCENT PROBE
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US20170045525A1

  公开（公告）日：2017-02-16

  [Problem] To provide the following: a novel fluorescent probe for detecting a compound, such as glutathione, that contains a —SH group; a detection method using said fluorescent probe; and a detection kit containing said probe. [Solution] A fluorescent probe for detecting a compound containing an —SH group, wherein the fluorescent probe comprises a compound represented by formula (I) or a salt thereof (In the formula, X represents Si(Ra)(R b ), Ge(R a )(R b ), Sn(R a )(R b ), C(R a )(R b ), or O (wherein R a and R b each independently represent a hydrogen atom or alkyl group); R 1 represents a hydrogen atom, or 1-4 identical or different substituents independently selected from the group consisting of a cyano group, alkyl group, carboxyl group, ester group, alkoxy group, amide group, and azide group, each of which may be optionally substituted; R 2 represents a hydrogen atom, halogen atom, hydroxyl group, cyano group, or an alkyl group, alkynyl group, alkoxy group, aryl, or heteroaryl, each of which may be optionally substituted; R 3 and R 4 each independently represent a hydrogen atom or 1-3 identical or different substituents independently selected from the group consisting of a hydroxyl group, halogen atom, or an alkyl group, sulfo group, carboxyl group, ester group, amide group and azide group, each of which may be optionally substituted; R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom or alkyl group, wherein, R 5 or R 6 , respectively together with R 3 , may form a ring structure including the nitrogen atoms bonded thereto, or R 7 or R 8 , respectively together with R 4 , may form a ring structure including the nitrogen atoms bonded thereto).

  提供以下内容：用于检测含有-SH基团的化合物（如谷胱甘肽）的新型荧光探针；使用所述荧光探针的检测方法；以及包含所述探针的检测试剂盒。解决方案：一种用于检测含有-SH基团的化合物的荧光探针，其中所述荧光探针包括由式（I）表示的化合物或其盐（在该式中，X表示Si（Ra）（Rb）、Ge（Ra）（Rb）、Sn（Ra）（Rb）、C（Ra）（Rb）或O（其中Ra和Rb各自独立地表示氢原子或烷基）；R1表示氢原子，或者独立选择自氰基、烷基、羧基、酯基、烷氧基、酰胺基和叠氮基的一致或不同的1-4个取代基，每个取代基可以选择性地被取代；R2表示氢原子、卤素原子、羟基、氰基或烷基、炔基、烷氧基、芳基或杂环芳基的一致或不同的取代基，每个取代基可以选择性地被取代；R3和R4各自独立地表示氢原子或独立选择自羟基、卤素原子或烷基、磺酰基、羧基、酯基、酰胺基和叠氮基的一致或不同的1-3个取代基，每个取代基可以选择性地被取代；R5、R6、R7和R8各自独立地表示氢原子或烷基，其中，R5或R6，分别与R3一起，可以形成包括与其相结合的氮原子的环结构，或者R7或R8，分别与R4一起，可以形成包括与其相结合的氮原子的环结构）。
• Development of Azo-Based Fluorescent Probes to Detect Different Levels of Hypoxia
  作者：Wen Piao、Satoru Tsuda、Yuji Tanaka、Satoshi Maeda、Fengyi Liu、Shodai Takahashi、Yu Kushida、Toru Komatsu、Tasuku Ueno、Takuya Terai、Toru Nakazawa、Masanobu Uchiyama、Keiji Morokuma、Tetsuo Nagano、Kenjiro Hanaoka

  DOI：10.1002/anie.201305784

  日期：2013.12.2

  Let it shine: New hypoxia‐sensitive fluorescent probes were developed; they consist of a rhodamine moiety with an azo group directly conjugated to the fluorophore. Because of an ultrafast conformational change around the NN bond, the compounds are nonfluorescent under normoxia. However, under hypoxia, the azo group is reduced, and a strongly fluorescent rhodamine derivative is released.

  让它发光：开发了新的对缺氧敏感的荧光探针；它们由若丹明部分和直接与荧光团偶联的偶氮基组成。由于NN键周围的构型发生了快速变化，因此该化合物在常氧下不发荧光。但是，在缺氧条件下，偶氮基被还原，并且释放出强荧光的若丹明衍生物。
• Red fluorescent scaffold for highly sensitive protease activity probes
  作者：Yu Kushida、Kenjiro Hanaoka、Toru Komatsu、Takuya Terai、Tasuku Ueno、Kengo Yoshida、Masanobu Uchiyama、Tetsuo Nagano

  DOI：10.1016/j.bmcl.2012.04.114

  日期：2012.6

  We have developed a novel red fluorescent dye, 2Me SiR600 (lambda(em) = 613 nm), in which the O atom of Rhodamine Green at the 10 position of the xanthene moiety is replaced with a Si atom, as a scaffold for probes to detect protease activity with extremely high S/N ratio. As proof of concept, we designed and synthesized probes for caspase-3 activity (Z-DEVD-SiR600) and leucine aminopeptidase activity (Leu-SiR600). Caspase-3-mediated cleavage of Z-DEVD-SiR600 resulted in a large bathochromic shift (93 nm) of the absorption maximum and a 432-fold fluorescence enhancement. (C) 2012 Elsevier Ltd. All rights reserved.